deoxycortisone   Click here for help

GtoPdb Ligand ID: 3450

Synonyms: 21-deoxycortisone
Compound class: Metabolite or derivative
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 71.44
Molecular weight 344.2
XLogP 0.75
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C1CCC2(C(=C1)CCC1C2C(=O)CC2(C1CCC2(O)C(=O)C)C)C
Isomeric SMILES O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2C(=O)C[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C
InChI InChI=1S/C21H28O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-16,18,25H,4-9,11H2,1-3H3/t15-,16-,18+,19-,20-,21-/m0/s1
InChI Key PUKLDDOGISCFCP-JSQCKWNTSA-N
Natural/Endogenous Targets
Target
Glucocorticoid receptor
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Rank order of potency at Glucocorticoid receptor cortisol, corticosterone >> aldosterone, deoxycortisone 1
Targets where the ligand is described in the comment field
Target Comment
CYP11B1 Converts deoxycortisone and 11-deoxycortisol to cortisone and cortisol, respectively. Loss-of-function mutations are associated with familial adrenal hyperplasia and hypertension.
CYP21A2 Converts progesterone and 17α-hydroxyprogesterone to deoxycortisone and 11-deoxycortisol, respectively